Sodium Hydroxide → HCID 69357330, compound

HRID 852544Notes

Reaction equation

HRID 852544 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH3:16])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH3:16])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68538880HCID 68538880, compound

Product 1

HCID 69357330HCID 69357330, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-ethoxy-isophthalic acid dimethyl ester (D43) (22 g, 92.4 mmol, 1 equiv) in MeOH (440 ml) was added 1N aqueous NaOH solution (87.8 ml, 87.8 mmol, 0.95 equiv) and the resulting solution was stirred at room temperature for 17 h. Most of the MeOH was removed in vacuo and the residue was partitioned between AcOEt and 1N aqueous NaOH solution. The aqueous layer was extracted with AcOEt, acidified to pH 1 and re-extracted with AcOEt. The second organic extract was dried over MgSO4 and concentrated in vacuo to give 5-ethoxy-isophthalic acid monomethyl ester (D45) (17 g, 82%) as a white solid. [M+H+ NH3]+=242.0, RT=2.79 min

Workup

  1. customMost of the MeOH was removed in vacuo
  2. customthe residue was partitioned between AcOEt and 1N aqueous NaOH solution
  3. extractionThe aqueous layer was extracted with AcOEt
  4. extractionre-extracted with AcOEt
  5. extractionThe second organic extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78fa2a39409a4fab9a8b2293e0d49f36
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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